Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear <i>n</i>-Alkyl Esters of Dicarboxylic Acids

Lipp, S. V.; Krasnykh, E. L.; Verevkin, Sergey P.

doi:10.1021/je100231g

Cited by 22 publications

(14 citation statements)

References 21 publications

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“…40−48 Early literature on the vapor pressure of DEM consists of two points over a relatively wide range from Anschutz and Reitter 49 at T = (360.25 to 471.05) K and a larger data set at T = (314.7 to 463.8) K by Heiber and Riendl. 50 Recent work by Lipp et al 51 extended the range of experimental data for DEM to T = (283.8) K, although those results differ from earlier work by Verevkin et al 52 The authors of the more recent work, including Verevkin, attributed that difference to lower sample purity in the earlier work and recommended disregarding the earlier results. Xu 429.57) K. 53 A large number of ambient-and reduced-pressure boiling points are available for DEM.…”

Section: ■ Introductionmentioning

confidence: 94%

Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate

et al. 2014

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Triethyl phosphate (TEPO,, tri-npropyl phosphate (TPPO,, and diethyl malonate (DEM, are of considerable interest to the chemical defense community as nontoxic simulants for toxic chemical warfare agents. Vapor pressure data have been measured for TEPO at T = (271.25 to 480.15) K, for TPPO at T = (263.15 to 527.61) K, and for DEM at T = (265.15 to 471.25) K using a variety of standard methods that have been modified as necessary. The new data extend the range of vapor pressure data previously reported in the literature for each of the title compounds to subambient temperatures and to lower pressures by approximately 3 orders of magnitude for TEPO, 5 orders of magnitude for TPPO, and 1 order of magnitude for DEM. Vapor pressure data and derived properties, including volatility and temperature-dependent heats of vaporization are reported for TEPO, TPPO, and DEM along with comparisons to chemical warfare agent materials.

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Section: ■ Introductionmentioning

confidence: 94%

Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate

et al. 2014

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“…Further collective sources have been used to complement -and compare -the experimental data [8,14,[23][24][25][26][27][28][29][30][31]. In addition, vapour-pressure data have been published specifically for various saturated and unsaturated hydrocarbons , alcohols [54][55][56][57][58][59], phenols [60,61], alkyl-and arylethers [62][63][64][65], acetals [66,67], carboxylic acids [68][69][70][71][72], carboxylic halides [73], carboxylic esters and lactones [74][75][76][77][78][79][80][81][82][83][84][85][86][87], carbonates [88][89][90]…”

Section: Sources Of Vapor-pressure Datamentioning

confidence: 99%

Calculation of the Vapour Pressure of Organic Molecules by Means of a Group-Additivity Method and their Resultant Gibbs Free Energy and Entropy of Vaporization at 298.15K

Naef¹,

Acree²

2021

Preprint

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The calculation of the vapour pressure of organic molecules at 298.15K is presented using a commonly applicable computer algorithm based on the group-additivity method. The basic principle of this method rests on the complete breakdown of the molecules into their constituting atoms, further characterized by their immediate neighbour atoms. The group contributions are calculated by means of a fast Gauss-Seidel fitting algorithm using the experimental data of 2036 molecules from literature. A ten-fold cross-validation procedure has been carried out to test the applicability of this method, which confirmed excellent quality for the prediction of the vapour pressure, expressed in log(pa), with a cross-validated correlation coefficient Q2 of 0.9938 and a standard deviation  of 0.26. Based on these data, the molecules' standard Gibbs free energy G°vap has been calculated. Furthermore, using their enthalpies of vaporization, predicted by an analogous group-additivity approach published earlier, the standard entropy of vaporization S°vap has been determined and compared with experimental data of 1129 molecules, exhibiting excellent conformance with a correlation coefficient R2 of 0.9598, a standard error  of 8.14 J/mol/K and a medium absolute deviation of 4.68%.

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“…data points [25,[73][74][75][76][77][78][79][80][81][82][83]). For Δ of acids, measurements were sourced which correspond to an infinitely dilute gas (as computed in [25]), which corresponds to the gas we simulate.…”

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confidence: 99%

Improving force field accuracy by training against condensed phase mixture properties

Boothroyd

Madin

Mobley

et al. 2022

Preprint

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Developing a sufficiently accurate classical force field representation of molecules is key to realizing the full potential of molecular simulation as a route to gaining fundamental insight into a broad spectrum of chemical and biological phenomena. This is only possible, however, if the many complex interactions between molecules of different species in the system are accurately captured by the model. Historically, the intermolecular van der Waals (vdW) interactions have primarily been trained against densities and enthalpies of vaporization of pure (single-component) systems, with occasional usage of hydration free energies. In this study, we demonstrate how including physical property data of binary mixtures can better inform these parameters, encoding more information about the underlying physics of the system in complex chemical mixtures. To demonstrate this, we re-train a select number of the Lennard-Jones parameters describing the vdW interactions of the OpenFF 1.0.0 (Parsley) fixed charge force field against training sets composed of densities and enthalpies of mixing for binary liquid mixtures as well as densities and enthalpies of vaporization of pure liquid systems, and assess the performance of each of these combinations. We show that retraining against the mixture data almost universally improves the force field's ability to reproduce both pure and mixture properties, reducing some systematic errors that exist when training vdW interactions against properties of pure systems only.

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Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids

Cited by 22 publications

References 21 publications

Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate

Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate

Calculation of the Vapour Pressure of Organic Molecules by Means of a Group-Additivity Method and their Resultant Gibbs Free Energy and Entropy of Vaporization at 298.15K

Improving force field accuracy by training against condensed phase mixture properties

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